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Human Metabolome Database Version 3.5

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Showing metabocard for 13,14-Dihydro PGF2a (HMDB04239)

Record Information
Version 3.5
Creation Date 2006-08-13 09:00:41 -0600
Update Date 2013-02-08 17:13:07 -0700
HMDB ID HMDB04239
Secondary Accession Numbers None
Metabolite Identification
Common Name 13,14-Dihydro PGF2a
Description 13,14-dihydro PGF2a is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207 Link_out)Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (5Z,9-alpha,11-alpha,15S)-9,11,15-trihydroxy-Prost-5-en-1-oate
  2. (5Z,9-alpha,11-alpha,15S)-9,11,15-trihydroxy-Prost-5-en-1-oic acid
  3. 13,14-Dihydro-pgf2-alpha
  4. 13,14-Dihydrodinoprost
  5. 13,14-Dihydroprostaglandin F2-alpha
  6. 13,14-Dihydroprostaglandin F2alpha
  7. 7-(3,5-Dihydroxy-2-(3-hydroxyoctyl)cyclopentyl)-5-Heptenoate
  8. 7-(3,5-Dihydroxy-2-(3-hydroxyoctyl)cyclopentyl)-5-Heptenoic acid
Chemical Formula C20H36O5
Average Molecular Weight 356.4968
Monoisotopic Molecular Weight 356.256274262
IUPAC Name (5E)-7-[3,5-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]hept-5-enoic acid
Traditional IUPAC Name (5E)-7-[3,5-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]hept-5-enoic acid
CAS Registry Number 27376-74-5
SMILES CCCCCC(O)CCC1C(O)CC(O)C1C\C=C\CCCC(O)=O
InChI Identifier InChI=1S/C20H36O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,15-19,21-23H,2-3,5-6,8-14H2,1H3,(H,24,25)/b7-4+
InChI Key LLQBSJQTCKVWTD-QPJJXVBHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Prostaglandins and related compounds
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • Carbocyclic Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Carboxylic Acid
  • Cyclic Alcohol
  • Secondary Alcohol
Direct Parent Prostaglandins and related compounds
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 2.183 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.14 g/L ALOGPS
LogP 4.10 ALOGPS
LogP 2.82 ChemAxon
LogS -3.41 ALOGPS
pKa (strongest acidic) 4.31 ChemAxon
pKa (strongest basic) -1.3 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 97.99 A2 ChemAxon
Rotatable Bond Count 13 ChemAxon
Refractivity 99.51 ChemAxon
Polarizability 42.47 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023344
KNApSAcK ID Not Available
Chemspider ID 4938997 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04239 Link_out
Metagene Link HMDB04239 Link_out
METLIN ID Not Available
PubChem Compound 6434009 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available